One-pot asymmetric synthesis of either diastereomer of tert-butanesulfinyl-protected amines from ketones

Jessica Tanuwidjaja; Hillary M Peltier; Jonathan A Ellman

doi:10.1021/jo0616512

One-pot asymmetric synthesis of either diastereomer of tert-butanesulfinyl-protected amines from ketones

J Org Chem. 2007 Jan 19;72(2):626-9. doi: 10.1021/jo0616512.

Authors

Jessica Tanuwidjaja¹, Hillary M Peltier, Jonathan A Ellman

Affiliation

¹ Department of Chemistry, University of California, Berkeley, California 94720, USA.

PMID: 17221983
DOI: 10.1021/jo0616512

Abstract

A one-pot method for the asymmetric synthesis of tert-butanesulfinyl-protected amines is described. Condensation of aryl alkyl and dialkyl ketones with tert-butanesulfinamide followed by in situ reduction with the appropriate reagent provides either diastereomer of the sulfinamide products in good yields and with diastereomeric ratios of up to 99:1.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amination
Amines / chemical synthesis*
Amines / chemistry
Ketones / chemical synthesis*
Ketones / chemistry
Molecular Conformation
Stereoisomerism
Sulfur Compounds / chemistry*

Substances

Amines
Ketones
Sulfur Compounds